By Aditi Shrikant
MarketWatch talked to experienced bartenders about ways to increase your chances of meeting someone in person
Sitting at the bar once is unlikely to net you a date – but by going more frequently, you’re more likely to find connection.
During the 18 years Kevin Cole has bartended at the Dead Poet in New York City, he has seen dozens of singles meet their person. A few years ago, he even officiated a marriage between two of them in the back of the bar.
“They were both nighttime regulars,” said Cole, 44. “They started off as friends. He was seeing someone and she was seeing someone. And then they ended up overlapping and being single at the same time.”
The bar meet-cute is a narrative that many singles strive for – not only because it feels like an early-aughts rom-com, but because dating apps can be draining.
Nearly 80% of dating-app users report being fatigued by the endless swiping, according to a recent Forbes Health Survey. More than half (51%) of Gen Z respondents said they are always or often feeling burnt out by apps like Tinder (MTCH), Bumble (BMBL) and Hinge. Forty-eight percent of millennials said the same.
In order to leave the apps and meet someone at a bar, though, you have to go to bars – a lot. That’s exactly what influencer Laurie Cooper challenged young women to do when she dubbed this month “Sit at the Bar September” in a recent TikTok. Cooper, a former “Real Housewives of New York” cast member and a real-estate agent in New York City, implored singles to “get off those dating apps and sit at the bar.”
“I’ll be checking in, girls,” she warned.
The advice is not month-specific or all that unusual. Sitting at a bar alone to meet other singles has long been promoted by dating coaches and even matchmaker and TV personality Patti Stanger of “Millionaire Matchmaker” fame, who has suggested women go to a steakhouse and read a book at the bar to meet men.
But going out alone is no cheap endeavor, especially in bigger cities where $15 drinks are common. For instance, the signature cocktails at Cooper’s top choice for “Sit at the Bar September,” the Carlyle Hotel on Manhattan’s Upper East Side, run from $28 to $36. Let’s say you get hungry while waiting for the one and decide to eat dinner: Solo diners spend, on average, $84 dollars per meal, according to 2024 data from OpenTable. That’s 48% more than those dining with others. Do this twice a week and you’re spending almost $700 per month to maybe, potentially meet someone who you might be able to date.
So how do you make going out alone worth your time and money? MarketWatch talked to experienced bartenders for insights. Rest assured, if you are one of the many Americans who has experienced dating-app fatigue, there are ways to increase your chances of meeting someone in person – and, therefore, make that extra spending even more worth it.
Pick the right bar
Tony Jimenez, 37, started bartending 18 years ago in San Juan, Puerto Rico. He then spent some time working in New York City before finally landing in Philadelphia, where he has been working for four years.
His advice is a little counterintuitive. If you want to meet someone, avoid popular or trendy bars, said Jimenez, who bartends at 1 Tippling Place and Bar Almanac.
“If a bar is popular, a lot of people will go there because it’s a popular bar, not to meet people,” he said.
It’s also best to avoid new bars, he said, for similar reasons: Many people will just be there to see if it lives up to the hype.
“It’s important that a bar has been there for at least a while,” he said. “I’d say four to five years.”
He suggests finding neighborhood spots with regulars who you enjoy.
“Those tend to be the bars where you bump into people more frequently,” he said. “It’s a meeting place for the community. It’s what a third space is supposed to be.”
The layout of the space can influence whether it’s easy to chat up a stranger, too. A curved bar where you can see everyone’s faces, for example, encourages mingling more than a straight-across one. And, of course, ample bar seating is a must.
Cole adds that you should go places that align with your interests.
“If you just go to a sports bar, you’re going to have a connection with a Mets fan,” he said. “You already have one thing in common.”
Conversely, if you don’t like shooting pool, maybe don’t go to a bar with a bunch of pool tables.
Ditch the laptop – and the job-interview questions
More important than picking the right bar might be how you present yourself.
Bringing a book, Jimenez said, is a “double-edged sword.”
“It is a conversation starter in the same way it can be a conversation stopper,” he said. “It could be an entry point to ask about the book. Or people could not talk to you because you’re reading a book.”
Being on your phone is OK, as long as what you’re doing seems like it could be interrupted, he said.
“If you’re playing a game, it looks different than if you’re reading an article on your phone,” he said. “You can interrupt an article, but if you interrupt someone playing a game, it feels intrusive.”
Laptops are the biggest deterrent to making a connection, Cole said: “Bringing a laptop says, ‘I’m working. I’m closed. Don’t talk to me.’”
Another crucial factor is your own willingness to mingle. While you need to be comfortable striking up a conversation, you don’t want to be overly inquisitive, Jimenez said.
“The people I’ve seen that fail the most are ones that treat it like a questionnaire where they are constantly asking too many questions about the other person, trying to see if they find something they like,” he said. “You’re not on a first date yet.”
Too many questions can make the other person feel like you’re trying to unearth a potential “red flag” too, Jiminez added, which can be off-putting.
You also don’t want to trauma-dump, Cole said.
“I see men and women just sharing too much,” he said. “It’s like, ‘I just met you – why are you telling me about your father when he passed away?’”
All you really should be doing is trying to see what commonalities you and another person might have.
For many of Cole’s patrons who end up in long-term relationships, it’s a slow burn. Conversation is kindled only after they run into each other a few times.
Sitting at the bar once is unlikely to net you a date – but by going more frequently and spending time getting to know others in your community, you’re more likely to find connection.
It’s a long-term investment that, if done right, could result in finding your soulmate.
If you’re just starting out on your money or career journey and have questions about how to navigate your finances, we want to hear from you. Write to Dollar Signs, MarketWatch’s new advice column, at dollarsigns@marketwatch.com.
-Aditi Shrikant
This content was created by MarketWatch, which is operated by Dow Jones & Co. MarketWatch is published independently from Dow Jones Newswires and The Wall Street Journal.
(END) Dow Jones Newswires
09-26-25 1601ET
Copyright (c) 2025 Dow Jones & Company, Inc.